13 January 2014 (online)
Potassium selenocyanate (KSeCN) is an easy-to-handle and readily available reagent. It is crystalline, colorless, highly hygroscopic, and air sensitive. Non-adequate storage may lead to its decomposition. This salt is soluble in protic solvents and non-protic polar solvent such as DMF, DMSO, NMP, and acetonitrile.
This reagent is commercially available and seldom prepared in the laboratory. It can be synthesized from metallic selenium and potassium cyanide in hot water or ethanol.
Methodologies employing KSeCN as the selenium source in the synthesis of organic selenocyanates and isoselenocyanates are practical and versatile. Because this functional group has a moderate reactivity, its conversion into other functional groups is highly interesting, allowing the formation of new C–Se bonds and the further generation of compounds with significant synthetic, pharmacological, and biological value.
- 1 Toshimitsu A. Organic Selenocyanates, Tellurocyanates and Related Compounds. In Patai's Chemistry of Functional Groups. John Wiley & Sons Ltd; Hoboken, New York: 2013
- 2 Sanmartín C, Palop JA, Romano B, Plano D. New Selenoderivatives as Antitumoral Agents in Prostate Cancer – Original Scientific Reports and Case Studies. Spiess PE. InTech; Winchester: 2011: 153-170
- 3 Reddy KH. V, Reddy VP, Madhav B, Shankar J, Nageswar YV. D. Synlett 2011; 1268
- 4 Kumar AV, Reddy VP, Reddy CS, Rao KR. Tetrahedron Lett. 2011; 52: 3978
- 5 Bouchet LM, Peñéñory AB, Argüello JE. Tetrahedron Lett. 2011; 52: 969
- 6 Sato T, Nakamura I, Terada M. Eur. J. Org. Chem. 2009; 5509
- 7 Sharma AK, Hossain SU, He P, Peters JM, Amin S. Bioorg. Med. Chem. Lett. 2010; 20: 4050
- 8 Rashid Baig NB, Chandrakala RN, Sai Sudhir V, Chandrasekaran S. J. Org. Chem. 2010; 75: 2910
- 9 Kanakaraju S, Prasanna B, Chandramouli GV. P. J. Chem. Pharm. Res. 2012; 4: 2994
- 10 Koketsu M, Otsuka T, Swenson D, Ishihara H. Org. Biomol. Chem. 2007; 5: 613